Janus-Type ESIPT Chromophores with Distinctive Intramolecular Hydrogen-bonding Selectivity
Dr. Yahui Chen
State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemical Engineering, Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), Nanjing Tech University, 211816 Nanjing, China
Department of Chemistry and Nanoscience, Ewha Womans University, 03760 Seoul, Korea
New and Renewable Energy Research Center, Ewha Womans University, 03760 Seoul, Korea
These authors contributed equally to this work.
Search for more papers by this authorDr. Sheng Lu
State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemical Engineering, Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), Nanjing Tech University, 211816 Nanjing, China
These authors contributed equally to this work.
Search for more papers by this authorSyed Ali Abbas Abedi
Fluorescence Research Group, Singapore University of Technology and Design, 8 Somapah Road, 487372 Singapore, Singapore
These authors contributed equally to this work.
Search for more papers by this authorMinseok Jeong
Department of Chemistry and Research Institute for Natural Science, Korea University, 02841 Seoul, Korea
These authors contributed equally to this work.
Search for more papers by this authorDr. Haidong Li
School of Bioengineering, Dalian University of Technology, 2 Linggong Road, Hi-tech Zone, 116024 Dalian, China
Search for more papers by this authorProf. Myung Hwa Kim
Department of Chemistry and Nanoscience, Ewha Womans University, 03760 Seoul, Korea
New and Renewable Energy Research Center, Ewha Womans University, 03760 Seoul, Korea
Search for more papers by this authorCorresponding Author
Prof. Sungnam Park
Department of Chemistry and Research Institute for Natural Science, Korea University, 02841 Seoul, Korea
Search for more papers by this authorCorresponding Author
Prof. Xiaogang Liu
Fluorescence Research Group, Singapore University of Technology and Design, 8 Somapah Road, 487372 Singapore, Singapore
Search for more papers by this authorCorresponding Author
Prof. Juyoung Yoon
Department of Chemistry and Nanoscience, Ewha Womans University, 03760 Seoul, Korea
Search for more papers by this authorCorresponding Author
Prof. Xiaoqiang Chen
State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemical Engineering, Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), Nanjing Tech University, 211816 Nanjing, China
Search for more papers by this authorDr. Yahui Chen
State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemical Engineering, Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), Nanjing Tech University, 211816 Nanjing, China
Department of Chemistry and Nanoscience, Ewha Womans University, 03760 Seoul, Korea
New and Renewable Energy Research Center, Ewha Womans University, 03760 Seoul, Korea
These authors contributed equally to this work.
Search for more papers by this authorDr. Sheng Lu
State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemical Engineering, Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), Nanjing Tech University, 211816 Nanjing, China
These authors contributed equally to this work.
Search for more papers by this authorSyed Ali Abbas Abedi
Fluorescence Research Group, Singapore University of Technology and Design, 8 Somapah Road, 487372 Singapore, Singapore
These authors contributed equally to this work.
Search for more papers by this authorMinseok Jeong
Department of Chemistry and Research Institute for Natural Science, Korea University, 02841 Seoul, Korea
These authors contributed equally to this work.
Search for more papers by this authorDr. Haidong Li
School of Bioengineering, Dalian University of Technology, 2 Linggong Road, Hi-tech Zone, 116024 Dalian, China
Search for more papers by this authorProf. Myung Hwa Kim
Department of Chemistry and Nanoscience, Ewha Womans University, 03760 Seoul, Korea
New and Renewable Energy Research Center, Ewha Womans University, 03760 Seoul, Korea
Search for more papers by this authorCorresponding Author
Prof. Sungnam Park
Department of Chemistry and Research Institute for Natural Science, Korea University, 02841 Seoul, Korea
Search for more papers by this authorCorresponding Author
Prof. Xiaogang Liu
Fluorescence Research Group, Singapore University of Technology and Design, 8 Somapah Road, 487372 Singapore, Singapore
Search for more papers by this authorCorresponding Author
Prof. Juyoung Yoon
Department of Chemistry and Nanoscience, Ewha Womans University, 03760 Seoul, Korea
Search for more papers by this authorCorresponding Author
Prof. Xiaoqiang Chen
State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemical Engineering, Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), Nanjing Tech University, 211816 Nanjing, China
Search for more papers by this authorAbstract
Excited-state intramolecular proton transfer (ESIPT)-based solid luminescent materials with multiple hydrogen bond acceptors (HBAs) remain unexplored. Herein, we introduced a family of Janus-type ESIPT chromophores featuring distinctive hydrogen bond (H-bond) selectivity between competitive HBAs in a single molecule. Our investigations showed that the central hydroxyl group preferentially forms intramolecular H-bonds with imines in imine-modified 2-hydroxyphenyl benzothiazole (HBT) chromophores but tethers the benzothiazole moiety in hydrazone-modified HBT chromophores. Imine-derived HBTs generally exhibit higher fluorescence efficiency, while hydrazone-derived HBTs show a reduced overlap between the absorption and fluorescence bands. Quantum chemical calculations unveiled the molecular origins of the biased intramolecular H-bonds and their impact on the ESIPT process. This Janus-type ESIPT chromophore skeleton provides new opportunities for the design of solid luminescent materials.
Conflict of interest
The authors declare no conflict of interest.
Open Research
Data Availability Statement
The data that support the findings of this study are available from the corresponding author upon reasonable request.
Supporting Information
As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors.
| Filename | Description |
|---|---|
| ange202311543-sup-0001-HBT-ABN.cif487.8 KB | Supporting Information |
| ange202311543-sup-0001-HBT-An.cif1.9 MB | Supporting Information |
| ange202311543-sup-0001-HBT-CPH.cif2.6 MB | Supporting Information |
| ange202311543-sup-0001-HBT-DPDA.cif337.6 KB | Supporting Information |
| ange202311543-sup-0001-HBT-IPA.cif543.7 KB | Supporting Information |
| ange202311543-sup-0001-HBT-MOA.cif2.2 MB | Supporting Information |
| ange202311543-sup-0001-HBT-NDPDA.cif3.9 MB | Supporting Information |
| ange202311543-sup-0001-HBT-PCH.cif631 KB | Supporting Information |
| ange202311543-sup-0001-HBT-PHZ.cif610.2 KB | Supporting Information |
| ange202311543-sup-0001-HBT-TFA.cif603.1 KB | Supporting Information |
| ange202311543-sup-0001-HBT-TFH.cif725.4 KB | Supporting Information |
| ange202311543-sup-0001-misc_information.pdf10.9 MB | Supporting Information |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
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